Shades of Grey
by locaxox
Summary: There's a thin line between love and hate, and Blair soon comes to realize that some lines aren't meant to be crossed. Dan/Blair/Chuck
1. Personality Clash

A/N: Hi everyone, and welcome to my story, Shades of Grey. This is a little experimental piece of mine, which I was dying to write after the last episode of Gossip girl. This story will be about 20 chapters, and takes place after 2x08 Pret-a-poor-Jenny. I haven't decided who the end couple is yet, Blair/Dan or Blair/Chuck.

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**Chapter one: Personality clash**

Blair pushed the straw around her cold drink while staring at her crimson nails in boredom. Starbucks was becoming increasingly dull by the minute, and Blair kept replaying the events of last night in her head. Normally, she would have her best friend, Serena with her, and they would be sipping their usual iced mocha's with whipped cream, but Serena was spending time with Aaron. Therefore, Blair buried her head in a magazine, while pondering over her non-existent relationship with Chuck and lightly sipping her beverage. She had to wonder, if she told Chuck she loved him, would they be together? After all, Chuck didn't entirely seem convinced when he gave that speech about their doomed relationship. Blair shouldn't have listened to Humphrey's stupid advice in the first place; she didn't need Brooklyn trash teaching her about love.

_Who would want to see Chuck and Blair holding hands and going to the movies anyway?_ Blair thought moodily, in response to her vivid memory of Chuck mocking the traditional actions of couples.

Rising from her chair, Blair swiveled around blindly and collided with a solid figure. In a flash, the contents of her latte drenched her designer coat, also managing to dampen the majority of her hair.

"Great," Blair muttered under her breathe. Just her luck. Wiping the mess up with napkins, she locked eyes with the culprit, only to find Dan Humphrey lying on the floor, wincing in pain. Trying to regain her balance, Blair glared daggers at him, while thinking of a million different ways in which she could ruin his life. Out of all people, it had to be the person that ruined what should have been the most romantic night of her life. Despite her fury towards him, Blair couldn't help but wonder what her best friend was thinking when she dated him. His hair was disorderly, and his clothing was so casual and unkempt that it made Blair want to scream.

"Oh, god, sorry Blair… I didn't mean-" Glowering at the person before her, Blair grabbed Dan's hair, pleased to see him gasp in surprise. Dragging him outside, Blair wasn't aware of onlookers pulling out their phones, most likely to inform gossip girl of Blair's sudden outburst.

"Ok, cabbage patch, here's the thing," Blair spoke venomously. "I was planning social suicide, but then I remembered you have no friends. Pull another stunt like that again, and I will ruin you." Dan stood there quietly, shifting his weight from one leg to the other, occasionally casting her mocking glances. Once she had finished her rant, Dan decided to speak.

"Um, Waldorf, don't you think you're over reacting?" Dan shrugged nonchalantly.

Blair rolled her eyes in disdain. "You know cabbage patch, for someone that's meant to be smart, you sure are dumb." Noticing the confusion in his eyes, Blair decided to elaborate. "If it weren't for you, Chuck and I would be together."

Dan just stood there, comprehension evident in his features. After all, what she was saying was true, but he had good reason for his actions. Dan tried to think of a response to her remark. However, it didn't matter, because Blair shook her head, cutting him off from anything he had to say. Dan looked at her in disbelief. Could he see tears in her eyes?

"You know what Humphrey? Just forget it. I'll send you the dry cleaning bill." With those final words, she stormed off.

* * *

Any doubt that Dan had in his mind about Blair's love for Chuck was gone. Who was he to judge the complicated relationships of the upper-east side anyway? Maybe it was the way she looked at him helplessly, that made Dan feel extremely guilty. However, the thought of her being melodramatic had also crossed his mind. Sighing in defeat, he pulled out his phone, and punched the digits of Serena's number in.

"Hello," a cheery female voice answered.

"Hey, Serena its Dan…" The palms of Dan's hands were beginning to perspire slightly, as he contemplated what to say next. After a few seconds, he came to the conclusion that it was best to be blunt."I want to get back on Blair's good side."

He winced as the words left his mouth. Maybe a little too blunt. Why should he have to make things up to a girl who thought he was a piece of dirt on her shoe? No… he wanted to feel less guilty about upsetting her. That was it? Right? Besides, since when was he ever on Blair's good side?

"Ok," Serena replied in a surprise. "But Dan, I thought you said the other night that you didn't care about Blair, and you were only giving her advice to help our friendship."

"I know, that's true, but no one deserves to have coffee spilt on them the day after a confrontation with Chuck," Dan paused briefly, preparing for the storm that was about to come. "Actually I'm not exactly sorry for the bad advice..."

"Dan!" _Ok, Maybe the wrong words,_ Dan thought wearily. He didn't react well under pressure, but it was true. Chuck and Blair had toyed with his best friend, and Vanessa even declared that Chuck was the more human of the two. "Firstly, she was wearing her favorite Versace coat today," Serena practically groaned into the phone. "And secondly, did Vanessa tell you what she did for Blair to get that angry with her?

"No," Dan said frowning. "What could Vanessa possibly do to get that sort of treatment from Chuck and Blair?"

"I'll let you talk about that with her when you go over and apologize," Serena answered instantly, as if it were the simplest thing in the world. "Look, Dan, B isn't that bad. If she sees you're making an effort, she'll be a lot nicer."

Dan's brain was working overtime. He sincerely doubted that Blair could even smile at him, let alone exchange pleasantries with 'Brooklyn trash'."Ok, I'll go over and apologize, but don't expect us to be friends," Dan affirmed. "And I thought you should know that I'm only doing this to put an end to my inner turmoil."

"Fine, but I think you'll be surprised at B. Tell me how it goes," Serena responded in a hurry. "Sorry Dan, Aaron's finally picked out a movie. Got to go."

Dan sighed in relief that the conversation ended, just before he could let his jealous ex-boyfriend side take over. Serena may have let go of him, but Dan knew it would be ages before he could let Serena go completely. Turning his i-pod on full blast, Dan tried to forget that he was traveling an extra half hour for some girl who hadn't even called him by his first name. He had been to her place, once, when they were plotting against Georgina. 

_At least I know where she lives,_ Dan reflected vaguely. Etched into his memory, was a large building worth enough money to feed his family for two years. Yep, he wouldn't get lost. Slightly rolling his eyes, Dan exited the train at the next stop, and hopped onto another platform, waiting for the transportation that would take him back towards the Upper East Side.

"To end the inner turmoil Humphrey," he kept repeating to himself when he started questioning his intentions of apologizing to Blair.

* * *

Blair strolled down random isles, eagerly awaiting a mystery outfit that would hopefully put and end to her miserable day. Mentally, she made a note to never visit the tedious boutique laid before her; the clothing was poorly sewn, and the fashion was seasons behind. Nothing seemed to be going right for Blair today. Turning on her heel, she exited the shop and retreated back to the limo that was parked outside waiting for her.

The sight of her coffee stained designer coat ruined the normally satisfying experience of relaxing into the limo's comfy leather seats. Blair frowned at the earlier occurrence today, when Humphrey had nearly reduced her to tears. Her accusation towards him, concerning Chuck may have been a tad unreasonable, but Blair wasn't one to apologize. Especially to some judgmental Brooklyn boy, whose best friend was a cabbage patch doll. Now, strangling Humphrey had to be added to her to-do list, along with discussing last night with Chuck, and getting into Yale.

Blair suddenly felt the limo come to a halt, therefore concluding that she was at her destination. Home. Gathering her Gucci bag, along with her coat, Blair managed to gracefully depart her means of transportation and sauntered towards her house. "Dorota," she called out bossily, after unlocking their giant wooden door. "I need you to run an errand for me-" her words were cut short when a familiar face came into view.

"Cabbage Patch?" Blair questioned, so surprised that she failed to appear angry at the person in front of her. Suddenly realizing her mistake, she hastily crossed her arms, and raised an eyebrow in distain. "What are you doing here?"

Dan tried carefully to choose his words, as she looked at him in anticipation. "Um, your maid let me in," he stated lamely. "I'm here… to apologize for your coat, I'll um… take it with me to the dry cleaners."

Blair rolled her eyes at his tendency of rambling. "My three-hundred dollar Versace coat is not going anywhere near Brooklyn. I'm scared of what you peasants might do to it." Blair knew she was treating him worse than she ever had, but she didn't care; he deserved every word. She could tell that he was affronted by the look on his face.

"I'd rather be a peasant as opposed to a rich upper-class snob, who contributes nothing and takes pleasure in ruining people's lives," Dan growled in frustration, as he already started towards the door. It amazed him that before last night, he actually thought Blair could be ok. "Oh and by the way, I don't pity you and your situation with Chuck. Not after what you did to Vanessa."

Walking towards the door, Dan was astonished to hear a small laugh coming from behind him. "Vanessa deserved what she got," Blair spoke simply, as Dan turned around to face her again. "She blackmailed me with that picture of Marcus and the Duchess."

Dan's eyebrows knitted in confusion. "But, Vanessa-"

"She's no an angel Cabbage patch, contrary to you deluded belief," Blair smirked slyly, and put her game face into play. "I know that you deliberately told me what you did to ruin what could have been between me and Chuck." Blair, much to her own surprise, was slightly disappointed when she saw the truth staring back at her. The fact that he was from Brooklyn made Blair trust him slightly more than she would with any of the girls in her posse. It wasn't like he had the ability to spread gossip, which was a small comfort to Blair. Humphrey was impossible to figure out. Not that she'd want to.

"Why would Serena tell you that?" Dan inquired with confusion as to why Serena would want to cause a dispute.

"Serena's my best friend. Remember? You're just the ex-boyfriend." Blair snidely commented.

"I'm sorry for any damage I caused Waldorf." Dan couldn't believe those words had left his mouth, but he found himself apologizing to Blair for the second time that day. "I'm sure Chuck will come to his senses," he tried to reassure her.

Blair stared at him blankly. Being infuriated with him was proving to be difficult, when he seemed so calm and sincere. Knowing deep down that the outcome for her and Chuck might have been the same with or without Humphreys words made Blair feel even guiltier. Just as he was about to leave, Blair gave into her conscience. "Humphrey." Watching a small smile outline her lips, Dan observed her change in attitude. "Don't worry about the coat. I'm sure Dorota can take care of it."

Taking into account the two factors of Blair nearly smiling, and letting him off the hook with her coat, Dan knew that his work here was finished. Awkwardly leaving the Waldorf residence with a slightly new perspective on a certain person, he felt a weight lift from his chest.

* * *

_A/N: Coming soon... Blair/Chuck interaction and Gossip girl posts :). Good? Bad? Should I continue?  
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	2. A Charity Event

**Chapter Two: A charity event**

"You look fine Blair," Serena commented, as her best friend fondled over outfits that would best 'suit her figure.' Rolling her eyes, she sat up as Blair demanded she look at the current blue dress she was sporting. "I repeat Blair, although Chuck knows fashion, he won't care what colour you wear."

Blair sighed at her best friends comment while inspecting herself in the mirror for what must be the hundredth time. "You don't understand though S, Bass industries is hosting the occasion, and I need to make a good impression on his dad. You know how much Chuck cares what he thinks."

Serena observed her friend's obsessive behavior, in interest. "Ok, I hate to point this out, but Bart's already met you. Quite a few times."

"It's never too late to make new first impressions though, is it?" Blair frowned at Serena's failure to realize the gravity of the situation. "Besides, you're the step-daughter."

"And what's that supposed to mean?" Serena scoffed in slight amusement.

"It means that you can basically waltz in there, destroy the charity event, and he wouldn't even bate and eyelash."

"So not true, he's been going on all week about this thing and our behavior," Serena said, before mimicking her step-father, much to Blair's amusement. She then turned to Blair on a serious note. "Dan and I were talking today…"

Blair's head immediately perked up in mention of the distasteful Brooklyn boy Serena formally knew as her ex. "Don't tell me he's coming tonight." Serena smiled apologetically under the stern gaze of her best friend. "Serena!" Blair exclaimed. "Why?"

"I had nothing to do with it. Vanessa was involved in the charity work, and she invited him," Serena shrugged in her own defense. "But I want you to try and be civil tonight."

"How many of these charity things does that Brooklyn troll go to?"

"Blair…"

"Fine," she groaned loudly in discontent. "Good thing you dumped cabbage patch."

"He dumped me remember?" Serena sighed loudly, trying to ignore the sour topic at hand, while returning to Blair's huge pile of dresses spread out on the bed.

"It's no loss," Blair looked at Serena in with an air of obviousness about her. "Besides, you met Aaron through Humphrey, and it wouldn't take me a second to decide which one I'd choose." Picking up black garment with a corset bodice, Serena beamed in victory.

"You know Blair," she said holding it against her petite figure. "With the amount of energy you put into your Humphrey rants, anyone who isn't me might think you're in love with him." Serena teased while concluding that black isn't her colour.

"Ugh," Blair groaned in disgust. "Anyone who isn't you might need to get psychologically evaluated." Serena laughed at her best friend's reaction.

"You should totally try this on." Blair nodded her head in approval at Serena's choice, before having her waist tightly constricted in silky onyx colored material. The fact that Serena was still slightly bitter about her breakup with Dan, however, did not escape her attention.

"You are over him right?" Blair asked, slightly concerned.

"Of course," Serena lied convincingly.

"Then welcome back S," Blair smirked, pulling her into a hug.

* * *

Chuck had been sitting at the bar for the entire night, bored out of his wits. Watching Blair continually make a fool out of herself in front of his father was his only source of entertainment. Sipping his scotch sparingly, his lips then curled up in amusement, as he watched Lily give Blair a curious look. Probably because she was doing everything in her power for his father's acceptance, except literally kissing his asse. Oh how he shuddered at the thought.

Downing the rest of his drink, Chuck then approached Nate, who he had currently patched things up with. Although he was residing at the Humphrey residence, Chuck still made a point to spend school hours and weekends with his best friend.

"Nathanial," he stated, peering curiously at the girl next to him. "And Vanessa, I didn't know you would be here." Chuck watched her face redden slightly at his presence. He couldn't blame her either. She wasn't too impressed with him after learning he tried to seduce her.

"Pleasure," Chuck drawled, kissing her hand in a way that others would perceive as a gentleman like gesture. He saw the look of disgust in her eyes, before she walked off. Nate looked at him in confusion; he was completely oblivious as to what took place at the Van Der Woodsen house warming, and Chuck was quite content with leaving out the details.

"Want to get high?" he invited, sneaking a joint in Nate's hand. Screw the charity event.

"Na man, I can't," Nate protested. "I don't want Vanessa to see me like that."

"Since when do you let women run your life?" Chuck scoffed. "Besides, you and Brooklyn aren't official so you can do what you want."

"I want to make a good impression. Sorry," Nate apologized, returning Chuck's gesture of good will.

"Suit yourself then," Chuck muttered, pocketing both joints as Nate trailed after Vanessa.

His focus then returned to his father who seemed a very uncomfortable with all the attention he was receiving from Blair. "Time to break up the 'happy' duo," Chuck mumbled vaguely. In a few strides, Chuck sat himself next to Blair.

"What are you too talking about?"

"Chuck," Blair smiled genuinely.

"Blair," Chuck acknowledged, still slightly amused by her behaviour. "Can I talk to you?" Without waiting for a response, he then pulled Blair away from Bart, who seemed somewhat relieved to get rid of his son's clingy friend.

"Yes Chuck," Blair spoke, with a sweet smile, as he led them over to a deserted area. Chuck was not fooled at her sickly sweetness though; he knew that smile was reserved for getting what she wanted. He had to admit, if there was an equivalent of a female Chuck Bass, it would be her.

"I know what you're doing…" Chuck drawled in a bored voice. "Getting to me through my father. Not going to work."

"Now Chuck, how would you know that?" she asked, voice barely above a whisper. Edging closer to him, Blair's face reflected feigned innocence, and yet she looked as though she would devour him on the spot.

Chuck slightly nodded his head, finally realizing what she was after. He should have known that even without dating, Blair would want to keep their relationship physical. Eyeing her up and down, Chuck would have liked nothing more than to rip off her dress, and take her right then. But he knew better.

"We decided we would wait Blair, until we were both ready to be in a relationship."

"That…" Blair rubbed up against him. "Doesn't mean we can't do other things."

"We could," Chuck nodded appreciatively, thinking for a minute. Part of him wondered if Blair would miss him though, or the way he made her feel. Perhaps sex was better postponed until he knew for sure. "But unfortunately for you, I won't." Blair frowned in surprise, stepping back from him.

"Talking to my father, coming to a charity event in a dress like that," Chuck took another moment to appreciate how good she was on the eyes. "I just thought you might like to know that you look… desperate." With those final words, Chuck kissed her fore head tenderly. "Welcome to how I felt."

***

_I need to get some air_, Dan thought as he gazed at Serena and Aaron dancing closely. Looking for the nearest escape, he hastily exited the room.

The night was cold, and Dan immediately regretted his decision. As the fallen leaves swayed in the autumn wind, he felt a presence of another. Peering at a secluded corner, of the building, the familiar outline of Blair Waldorf came into view. Their eyes met, and quickly tried to hide the empty champagne bottle she was holding.

"Blair?" Dan inquired, approaching the figure.

"Humphrey," Blair greeted shortly.

"What are you doing out here?" Taking note of the empty bottle hidden behind her back, and her sad face, he came to the conclusion that she was wallowing in what seemed like self pity.

"It doesn't matter," Blair responded, getting up. "Whoa." She cradled her face in the palm of her hands. Grabbing her arm soothingly, Dan then guided Blair back to her sitting position. "I feel terrible."

"Um, Blair, I don't know how to tell you this but…" Dan stuttered. How was he going to tell Blair that she should stay seated, or risk public humiliation? She was obviously a little tipsy, which wouldn't do too well to her 'pristine' image. "I think you've had a little to drink."

"No shit," Blair said, looking at the champagne bottle in a pointedly manner.

"A in you're a little tipsy," Dan sighed. Great, he certainly hadn't imagined his night consisting of aiding Blair Waldorf.

"I'm fine cabbage patch," Blair slurred indignantly. "If anything, I'm not tipsy enough."

Dan glanced at the empty bottle of champagne. "Is that all you've had in the last hour?" Blair nodded her head.

"Wow Waldorf, you can certainly hold your liquor," Dan stated, while chuckling to himself. Not knowing whether to take it as sarcasm, Blair slapped him on the arm playfully, while trying to suppress a grin.

"It's cold out here," Blair complained, trying to rub her goosebumps away. Without hesitation, Dan placed his jacket on her bare arms, making him even more frozen. "Can we just go inside?" Blair gave him her best puppy dog eyes.

Dan stayed silent for a moment, thinking where he could take Blair to sober up. Then it came to him. "We can go inside… we just can't go back where everyone else is," he explained, talking to her as though she were a toddler.

"Why?" Blair frowned at Dan, as he helped her stand. Placing an arm around her waste, to support her, Dan ventured up the stairs, with Blair clinging onto him.

"Well we can't have you causing a scene now, can we?" Dan played along in a sing-song voice.

"Oh yeah," Blair smiled in realization.

Dan led Blair to the wine cellar, he had noticed at the beginning of the night. "I'm going to go to the kitchen and get you some stuff that will sober you up. I'll be back soon, just don't leave this room."

"Ok Dan," Blair giggled absent mindedly.

* * *

Dan re-entered the cellar with pots of coffee, water and bagels with cream cheese spread. Blair looked at him in amazement. "How'd…. you get all that?" she queried, tripping over her words.

"I've got my ways," Dan winked, placing the tray next to her. As he sat down Dan noticed a bottle of wine beside her, nearly halfway empty. "Christ Blair," he whined, nearly pulling his hair out in frustration. "Please tell me you didn't drink this."

The snigger that came from her lips was enough of an answer for him. Blair then sandwiched three bagels together with cream cheese spread, and forced a large section into her mouth. "Mmm," she appreciated. "Yummy."

Blair shamelessly chewed with her mouth open, and her face was covered in cream cheese as she munched away blissfully. One look at Blair shoveling down everything she could fit into her mouth, sent Dan laughing hysterically.

At first, Blair glanced up in confusion, but then started to join in. As the duo sat there, laughing over nothing, Dan all of a sudden became serious. "What's wrong?" he heard her ask.

"Nothing," he assured, staring at her skeptic expression.

"Dan," Blair pleaded with a silly expression. "Please tell me."

He thought about it logically. Perhaps he could tell her. She was drunk, so probably wouldn't remember it tomorrow. "Ok then," Dan started bravely. "I just had a moment when I remembered how Serena and I used to be like this."

"Does cabbage patch miss Serena?" Blair's smile turned into one of mock seriousness. "Because I think she misses you too."

Dan immediately looked over at Blair. "She said that?"

"Well…" Blair avoided his gaze. "No. But I can see it."

Dan looked down disappointedly, pouring Blair a cup of coffee. "So Waldorf, I'm wondering, why did you decide to get drunk at a public function?"

Her wide, brown eyes saddened, and focused her full attention on her mug of scorching caffeine. Dan then took note of her sudden change in demeanor. "You don't need to tell-"

"I don't think Chuck wants me anymore," Blair admitted, finally meeting his eyes with a look of vulnerability that nearly broke Dan's heart. She reminded him of a school girl, asking a teacher where she should go from here. "I threw myself at Chuck tonight, and tried so hard with his dad, but no avail." Blair continued on emotionally. "He told me that we should wait until we're older, but then I see him kissing Abrams hand and flirting with other girls."

Dan sighed, as a tear cascaded down her cheek. Blair violently coughed, and carelessly wiped the tear away, smudging her make up, still failing to look anything less than perfect.

"Chuck's a fool if he can't see how much you care for him," Dan tried to convince her.

"You think so?" Blair turned to look at him, awkwardly resting her head on his shoulder. "Nate didn't want me either." Dan found it unnecessary to point out that she brought it on herself by cheating with Chuck, so instead, he let Blair rest.

"Blair?" A few minutes later, Dan tried to wake her up, but she was passed out cold. Gently removing her head from his shoulder, he gathered the tray, and exited the cellar quietly, dumping the dishes in the kitchen.

Then returning, to keep an eye on Blair, Dan called Serena, informing her of Blair's whereabouts, and how she passed out, probably from alcohol.

Serena was there in a flash, after Dan explained what happened. After assessing their options, Dan and Serena came to the conclusion that she would take Blair home in a cab, after saying goodbye to everyone. While Dan called the cab and Serena said her goodbyes, he couldn't help but smile at the drunk, very different version of Blair.

"Thank you so much for doing this Dan," Serena repeated for the millionth time as they managed to get Blair into the taxi. "I know this isn't how you wanted to spent your night."

"No Problem," Dan answered honestly.

"Ok, well I'll see you are school tomorrow?" Serena asked, as she strapped Blair in and entered the cab herself.

"Yep," Dan said waving them off. Sighing in bewilderment, he then went back to join in with the 'festivities.' Dan would spend another three hours with a drunken Blair any day, rather then listen to the ramblings of snobby Upper east siders.


End file.
